If you right click it > properties > Compatibility > then choose windows 98/me and select run as admin does it help. Not sure if you tried it.
I asked about the specs wrong I meant to ask if you knew what the system requirements were to run the game. I was curious how old it was and if it was 16bit. I think only windows 8 32 bit can run a 16bit app. There are some emulators out there but I don't know if that is the issue.
When I get a few min, I am going to look into the USB issue to see if we can get it to work